cap. 5 Flashcards
(21 cards)
oxygen is ___ hybridized
sp3. it is tetrahedral
iupac for alcohols
- find longest C chain that contains -OH group
- number the chain where the -OH group is the lowest
- all substituents will be named and numbered in alphabetical order
enol
alkene that contains an alcohol group
hydroxy substituent
when -OH is a part of a higher priority compound, it will take on “hydroxy” in the name
phenol nomenclature
(benzic ring)
- -OH group is assumed to be on carbon 1
ortho- 1,2
meta- 1,3
para- 1,4
solubility of alcohols in water
small alcohols (methyl-tert butyle alcohol) are miscible, but larger ones are not
acidity of alcohols
pka- 15.5-18.0
acidity decreases when substitution on the alkyl group increases
- halogens and other electron-withdrawing groups increase the acidity
how to open an epoxide ring
- acid catalyzed (h3O+)
thiol
sulfur analogues of alcohols
HS-CH2CH2-OH
mercapto group
-SH
CH3-SH
methanethiol
thiols are (more/less) acidic than alcohols
more acidic.
thiols are commonly made by ___ reaction, so ___ (1°, 2°, 3°) alkyl halides work better
Sn2, primary
thiols can be ____ (reduced/oxidized) to form
oxidized to form disulfides. these can be reduced back to a thiol with a reducing agent.
oxidation in orgo
gain of O or O2, and X2, but it’s a loss of H2.
reduction
gain of H2 or H-. It’s a loss of O or O2, and loss of X2
when a 2° alcohol is oxidized, it becomes a
ketone
basically the opposite of reduction
chromic acid
Na2Cr2O7
chromic acid can oxidize 1° alcohols into
carboxylic acid
it’s a strong oxidizing agent, so it won’t stop at the aldehyde
PCC oxidizes 1° alcohols to
aldehydes
PCC oxidizes 2° alcohols to
ketones
